Second monoclinic polymorph of 2-(benzimidazol-2-yl)-6-methoxy­phenol

The asymmetric unit of the title compound, C₁₄H₁₂N₂O₂, contains four crystallographically independent mol­ecules. The crystal packing is stabilized by π–π, N—H...O and C—H...π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.008 Å
• R factor = 0.091
• wR factor = 0.223
• Data-to-parameter ratio = 12.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          8
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         28

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

2-(benzimidazol-2-yl)-6-methoxyphenol

Crystal data

C14H12N2O2	F(000) = 2016
Mr = 240.26	Dx = 1.382 Mg m^−3
Monoclinic, P2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yc	Cell parameters from 4994 reflections
a = 20.0313 (6) Å	θ = 1.1–25.0°
b = 12.0577 (4) Å	µ = 0.09 mm^−1
c = 20.0379 (7) Å	T = 100 K
β = 107.382 (2)°	Block, yellow
V = 4618.8 (3) Å^3	0.25 × 0.25 × 0.25 mm
Z = 16

Data collection

Brucker SMART APEX2 CCD diffractometer	8132 independent reflections
Radiation source: fine-focus sealed tube	5426 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.060
Detector resolution: 8.33 pixels mm^-1	θmax = 25.0°, θmin = 1.1°
ω scans	h = −21→23
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −11→14
Tmin = 0.964, Tmax = 0.977	l = −23→23
31231 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.091	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.223	H-atom parameters constrained
S = 1.16	w = 1/[σ^2(Fo^2) + (0.0176P)^2 + 23.9891P] where P = (Fo^2 + 2Fc^2)/3
8132 reflections	(Δ/σ)max < 0.001
653 parameters	Δρmax = 0.36 e Å^−3
0 restraints	Δρmin = −0.36 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1A	0.52164 (19)	0.1080 (3)	0.17727 (19)	0.0303 (9)
H1AB	0.4789	0.1137	0.1661	0.045*
O2A	0.6567 (2)	0.1128 (3)	0.2120 (2)	0.0388 (10)
N1A	0.3922 (2)	0.3884 (4)	0.1276 (2)	0.0293 (11)
H1AA	0.4045	0.4568	0.1280	0.035*
N2A	0.4013 (2)	0.2043 (4)	0.1400 (2)	0.0268 (10)
C1A	0.3307 (3)	0.2329 (5)	0.1140 (3)	0.0283 (13)
C2A	0.2711 (3)	0.1661 (5)	0.0978 (3)	0.0394 (15)
H2AB	0.2741	0.0894	0.1027	0.047*
C3A	0.2072 (3)	0.2198 (5)	0.0742 (3)	0.0444 (17)
H3AA	0.1664	0.1777	0.0631	0.053*
C4A	0.2019 (3)	0.3350 (5)	0.0665 (4)	0.0456 (17)
H4AA	0.1579	0.3675	0.0507	0.055*
C5A	0.2608 (3)	0.4022 (5)	0.0819 (3)	0.0381 (15)
H5AA	0.2579	0.4787	0.0763	0.046*
C6A	0.3243 (3)	0.3475 (5)	0.1062 (3)	0.0285 (13)
C7A	0.4358 (3)	0.2992 (4)	0.1477 (3)	0.0243 (12)
C8A	0.5118 (3)	0.3077 (5)	0.1709 (3)	0.0277 (13)
C9A	0.5473 (3)	0.4100 (5)	0.1795 (3)	0.0267 (13)
H9AA	0.5222	0.4760	0.1720	0.032*
C10A	0.6186 (3)	0.4118 (5)	0.1987 (3)	0.0322 (14)
H10A	0.6415	0.4798	0.2043	0.039*
C11A	0.6580 (3)	0.3155 (5)	0.2103 (3)	0.0339 (14)
H11A	0.7066	0.3188	0.2232	0.041*
C12A	0.6241 (3)	0.2148 (5)	0.2023 (3)	0.0288 (13)
C13A	0.5505 (3)	0.2097 (4)	0.1832 (3)	0.0244 (12)
C14A	0.7304 (3)	0.1118 (6)	0.2229 (4)	0.0449 (17)
H14A	0.7455	0.0374	0.2183	0.067*
H14B	0.7540	0.1390	0.2689	0.067*
H14C	0.7414	0.1585	0.1888	0.067*
O1B	0.07185 (19)	0.8545 (3)	0.3456 (2)	0.0302 (9)
H1BA	0.0293	0.8474	0.3356	0.045*
O2B	0.20576 (19)	0.8540 (3)	0.3802 (2)	0.0322 (9)
N1B	−0.0546 (2)	0.5729 (4)	0.3280 (2)	0.0276 (11)
H1BB	−0.0423	0.5043	0.3332	0.033*
N2B	−0.0455 (2)	0.7567 (4)	0.3226 (2)	0.0240 (10)
C1B	−0.1159 (3)	0.7293 (5)	0.3099 (3)	0.0270 (12)
C2B	−0.1747 (3)	0.7972 (5)	0.2949 (3)	0.0333 (14)
H2BB	−0.1709	0.8738	0.2923	0.040*
C3B	−0.2385 (3)	0.7464 (6)	0.2842 (3)	0.0406 (16)
H3BA	−0.2789	0.7894	0.2731	0.049*
C4B	−0.2438 (3)	0.6318 (6)	0.2898 (3)	0.0398 (16)
H4BA	−0.2877	0.6007	0.2836	0.048*
C5B	−0.1863 (3)	0.5625 (5)	0.3041 (3)	0.0370 (15)
H5BA	−0.1903	0.4860	0.3072	0.044*
C6B	−0.1223 (3)	0.6137 (5)	0.3134 (3)	0.0285 (13)
C7B	−0.0113 (3)	0.6610 (4)	0.3325 (3)	0.0230 (12)
C8B	0.0648 (3)	0.6542 (4)	0.3477 (2)	0.0221 (11)
C9B	0.1008 (3)	0.5532 (5)	0.3555 (3)	0.0296 (13)
H9BA	0.0765	0.4866	0.3506	0.036*
C10B	0.1724 (3)	0.5533 (5)	0.3706 (3)	0.0318 (14)
H10B	0.1960	0.4860	0.3746	0.038*
C11B	0.2101 (3)	0.6503 (5)	0.3798 (3)	0.0324 (14)
H11B	0.2586	0.6484	0.3908	0.039*
C12B	0.1755 (3)	0.7507 (4)	0.3727 (3)	0.0252 (12)
C13B	0.1026 (3)	0.7526 (4)	0.3551 (3)	0.0242 (12)
C14B	0.2804 (3)	0.8579 (6)	0.4056 (4)	0.0448 (17)
H14D	0.2953	0.9334	0.4152	0.067*
H14E	0.2996	0.8278	0.3710	0.067*
H14F	0.2963	0.8150	0.4478	0.067*
O1C	0.0718 (2)	0.3497 (3)	0.2146 (2)	0.0389 (10)
H1CA	0.0872	0.3455	0.2574	0.058*
O2C	0.0220 (2)	0.3368 (3)	0.0789 (2)	0.0408 (11)
N1C	0.1227 (2)	0.0753 (4)	0.3491 (2)	0.0293 (11)
H1CB	0.1182	0.0061	0.3383	0.035*
N2C	0.1204 (2)	0.2586 (4)	0.3367 (2)	0.0294 (11)
C1C	0.1466 (3)	0.2335 (4)	0.4080 (3)	0.0284 (13)
C2C	0.1679 (3)	0.3014 (5)	0.4662 (3)	0.0393 (15)
H2CB	0.1675	0.3782	0.4617	0.047*
C3C	0.1898 (3)	0.2515 (5)	0.5308 (3)	0.0379 (15)
H3CA	0.2042	0.2955	0.5707	0.046*
C4C	0.1910 (3)	0.1349 (5)	0.5379 (3)	0.0396 (15)
H4CA	0.2065	0.1040	0.5824	0.048*
C5C	0.1698 (3)	0.0659 (5)	0.4809 (3)	0.0323 (14)
H5CA	0.1701	−0.0109	0.4854	0.039*
C6C	0.1479 (3)	0.1178 (5)	0.4162 (3)	0.0299 (13)
C7C	0.1062 (3)	0.1613 (5)	0.3034 (3)	0.0266 (12)
C8C	0.0784 (3)	0.1505 (4)	0.2283 (3)	0.0250 (12)
C9C	0.0672 (3)	0.0470 (5)	0.1956 (3)	0.0300 (13)
H9CA	0.0769	−0.0174	0.2224	0.036*
C10C	0.0418 (3)	0.0397 (5)	0.1234 (3)	0.0343 (14)
H10C	0.0351	−0.0295	0.1019	0.041*
C11C	0.0263 (3)	0.1351 (5)	0.0833 (3)	0.0342 (14)
H11C	0.0090	0.1296	0.0349	0.041*
C12C	0.0362 (3)	0.2366 (5)	0.1140 (3)	0.0323 (14)
C13C	0.0623 (3)	0.2458 (5)	0.1869 (3)	0.0279 (13)
C14C	−0.0007 (4)	0.3314 (6)	0.0042 (3)	0.0552 (19)
H14G	−0.0091	0.4050	−0.0147	0.083*
H14H	−0.0431	0.2889	−0.0111	0.083*
H14I	0.0348	0.2965	−0.0118	0.083*
O1D	0.59027 (19)	0.6100 (3)	0.32521 (18)	0.0276 (9)
H1DA	0.5799	0.6164	0.2826	0.041*
O2D	0.6257 (2)	0.6156 (3)	0.46046 (19)	0.0331 (9)
N1D	0.5734 (2)	0.8880 (4)	0.1961 (2)	0.0274 (11)
H1DB	0.5767	0.9571	0.2072	0.033*
N2D	0.5741 (2)	0.7049 (4)	0.2079 (2)	0.0248 (10)
C1D	0.5612 (3)	0.7293 (4)	0.1366 (3)	0.0231 (12)
C2D	0.5524 (3)	0.6598 (5)	0.0802 (3)	0.0312 (13)
H2DB	0.5536	0.5831	0.0852	0.037*
C3D	0.5415 (3)	0.7107 (5)	0.0152 (3)	0.0355 (14)
H3DA	0.5352	0.6665	−0.0243	0.043*
C4D	0.5396 (3)	0.8261 (5)	0.0078 (3)	0.0344 (14)
H4DA	0.5315	0.8567	−0.0366	0.041*
C5D	0.5497 (3)	0.8967 (5)	0.0652 (3)	0.0309 (13)
H5DA	0.5495	0.9736	0.0609	0.037*
C6D	0.5601 (3)	0.8439 (5)	0.1292 (3)	0.0263 (12)
C7D	0.5803 (3)	0.8004 (4)	0.2405 (3)	0.0208 (11)
C8D	0.5963 (3)	0.8102 (4)	0.3168 (3)	0.0227 (12)
C9D	0.6087 (3)	0.9121 (4)	0.3518 (3)	0.0240 (12)
H9DA	0.6060	0.9776	0.3265	0.029*
C10D	0.6247 (3)	0.9156 (5)	0.4234 (3)	0.0266 (12)
H10D	0.6316	0.9837	0.4462	0.032*
C11D	0.6307 (3)	0.8187 (5)	0.4621 (3)	0.0298 (13)
H11D	0.6421	0.8220	0.5106	0.036*
C12D	0.6199 (3)	0.7174 (4)	0.4285 (3)	0.0247 (12)
C13D	0.6016 (3)	0.7126 (4)	0.3555 (3)	0.0241 (12)
C14D	0.6447 (3)	0.6154 (5)	0.5345 (3)	0.0375 (15)
H14J	0.6505	0.5403	0.5512	0.056*
H14K	0.6086	0.6507	0.5494	0.056*
H14L	0.6878	0.6550	0.5530	0.056*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.030 (2)	0.023 (2)	0.040 (2)	0.0009 (17)	0.0140 (18)	0.0000 (18)
O2A	0.033 (2)	0.032 (2)	0.051 (3)	0.0052 (19)	0.012 (2)	0.002 (2)
N1A	0.040 (3)	0.020 (3)	0.030 (3)	0.002 (2)	0.015 (2)	−0.004 (2)
N2A	0.028 (3)	0.025 (3)	0.028 (2)	0.004 (2)	0.009 (2)	−0.003 (2)
C1A	0.031 (3)	0.027 (3)	0.028 (3)	−0.002 (3)	0.013 (2)	−0.009 (2)
C2A	0.041 (4)	0.038 (4)	0.043 (4)	−0.006 (3)	0.019 (3)	−0.013 (3)
C3A	0.031 (4)	0.043 (4)	0.061 (4)	−0.006 (3)	0.016 (3)	−0.019 (3)
C4A	0.034 (4)	0.041 (4)	0.059 (4)	0.007 (3)	0.011 (3)	−0.015 (3)
C5A	0.043 (4)	0.030 (3)	0.041 (4)	0.003 (3)	0.013 (3)	−0.008 (3)
C6A	0.034 (3)	0.026 (3)	0.027 (3)	0.000 (3)	0.012 (2)	−0.013 (2)
C7A	0.030 (3)	0.026 (3)	0.019 (3)	0.003 (2)	0.011 (2)	−0.003 (2)
C8A	0.034 (3)	0.028 (3)	0.023 (3)	−0.001 (3)	0.010 (2)	−0.001 (2)
C9A	0.032 (3)	0.024 (3)	0.026 (3)	0.000 (2)	0.011 (2)	−0.001 (2)
C10A	0.038 (4)	0.030 (3)	0.030 (3)	−0.007 (3)	0.013 (3)	0.005 (3)
C11A	0.036 (3)	0.038 (4)	0.029 (3)	−0.004 (3)	0.012 (3)	−0.001 (3)
C12A	0.033 (3)	0.026 (3)	0.028 (3)	0.012 (3)	0.010 (2)	0.005 (2)
C13A	0.038 (3)	0.018 (3)	0.018 (3)	−0.006 (2)	0.010 (2)	0.001 (2)
C14A	0.024 (3)	0.051 (4)	0.059 (4)	0.005 (3)	0.012 (3)	0.003 (3)
O1B	0.024 (2)	0.022 (2)	0.045 (2)	0.0032 (16)	0.0100 (18)	0.0026 (18)
O2B	0.024 (2)	0.026 (2)	0.047 (2)	−0.0026 (17)	0.0106 (18)	0.0018 (18)
N1B	0.038 (3)	0.020 (2)	0.026 (2)	−0.004 (2)	0.011 (2)	−0.002 (2)
N2B	0.023 (2)	0.023 (3)	0.027 (2)	0.004 (2)	0.0095 (19)	−0.001 (2)
C1B	0.029 (3)	0.028 (3)	0.027 (3)	−0.001 (2)	0.014 (2)	−0.001 (2)
C2B	0.025 (3)	0.039 (4)	0.036 (3)	0.000 (3)	0.010 (3)	−0.009 (3)
C3B	0.032 (4)	0.053 (4)	0.037 (3)	0.001 (3)	0.011 (3)	−0.004 (3)
C4B	0.029 (3)	0.052 (4)	0.042 (4)	−0.014 (3)	0.015 (3)	−0.015 (3)
C5B	0.045 (4)	0.034 (4)	0.038 (3)	−0.016 (3)	0.020 (3)	−0.013 (3)
C6B	0.033 (3)	0.031 (3)	0.023 (3)	−0.005 (3)	0.012 (2)	−0.007 (2)
C7B	0.028 (3)	0.024 (3)	0.018 (3)	−0.001 (2)	0.009 (2)	0.005 (2)
C8B	0.029 (3)	0.022 (3)	0.017 (3)	0.000 (2)	0.009 (2)	0.004 (2)
C9B	0.036 (4)	0.025 (3)	0.029 (3)	0.005 (3)	0.010 (3)	−0.001 (2)
C10B	0.037 (4)	0.025 (3)	0.037 (3)	0.009 (3)	0.017 (3)	0.007 (3)
C11B	0.032 (3)	0.034 (3)	0.035 (3)	0.008 (3)	0.015 (3)	0.007 (3)
C12B	0.024 (3)	0.023 (3)	0.028 (3)	0.000 (2)	0.007 (2)	0.000 (2)
C13B	0.027 (3)	0.021 (3)	0.027 (3)	0.004 (2)	0.011 (2)	0.001 (2)
C14B	0.025 (3)	0.046 (4)	0.059 (4)	−0.010 (3)	0.006 (3)	−0.003 (3)
O1C	0.063 (3)	0.022 (2)	0.031 (2)	0.007 (2)	0.012 (2)	0.0030 (18)
O2C	0.060 (3)	0.031 (2)	0.029 (2)	0.003 (2)	0.010 (2)	0.0056 (19)
N1C	0.035 (3)	0.017 (2)	0.035 (3)	0.000 (2)	0.010 (2)	0.003 (2)
N2C	0.039 (3)	0.020 (3)	0.029 (3)	0.002 (2)	0.009 (2)	0.002 (2)
C1C	0.033 (3)	0.019 (3)	0.032 (3)	−0.001 (2)	0.006 (2)	−0.001 (2)
C2C	0.056 (4)	0.028 (3)	0.033 (3)	−0.002 (3)	0.012 (3)	−0.002 (3)
C3C	0.050 (4)	0.029 (3)	0.031 (3)	0.003 (3)	0.006 (3)	−0.001 (3)
C4C	0.044 (4)	0.040 (4)	0.037 (3)	0.005 (3)	0.014 (3)	0.007 (3)
C5C	0.042 (4)	0.019 (3)	0.036 (3)	0.005 (3)	0.011 (3)	0.004 (3)
C6C	0.030 (3)	0.027 (3)	0.030 (3)	0.002 (3)	0.006 (2)	0.001 (3)
C7C	0.024 (3)	0.025 (3)	0.029 (3)	0.000 (2)	0.005 (2)	0.002 (3)
C8C	0.023 (3)	0.023 (3)	0.031 (3)	−0.002 (2)	0.010 (2)	0.003 (2)
C9C	0.035 (3)	0.027 (3)	0.030 (3)	−0.004 (3)	0.013 (3)	−0.004 (3)
C10C	0.039 (4)	0.033 (3)	0.032 (3)	−0.004 (3)	0.014 (3)	−0.004 (3)
C11C	0.044 (4)	0.035 (4)	0.028 (3)	−0.010 (3)	0.017 (3)	−0.002 (3)
C12C	0.036 (3)	0.034 (4)	0.031 (3)	0.002 (3)	0.016 (3)	0.009 (3)
C13C	0.026 (3)	0.024 (3)	0.037 (3)	−0.001 (2)	0.013 (3)	−0.003 (3)
C14C	0.074 (5)	0.057 (5)	0.031 (3)	0.001 (4)	0.010 (3)	0.016 (3)
O1D	0.041 (2)	0.019 (2)	0.0233 (19)	0.0012 (17)	0.0108 (17)	0.0012 (16)
O2D	0.047 (3)	0.026 (2)	0.028 (2)	0.0038 (18)	0.0132 (18)	0.0056 (17)
N1D	0.032 (3)	0.026 (3)	0.025 (2)	0.005 (2)	0.009 (2)	0.002 (2)
N2D	0.028 (3)	0.026 (3)	0.024 (2)	0.001 (2)	0.0132 (19)	0.002 (2)
C1D	0.025 (3)	0.022 (3)	0.025 (3)	0.004 (2)	0.011 (2)	0.002 (2)
C2D	0.034 (3)	0.028 (3)	0.033 (3)	0.005 (3)	0.014 (3)	−0.001 (3)
C3D	0.044 (4)	0.040 (4)	0.025 (3)	0.002 (3)	0.015 (3)	−0.006 (3)
C4D	0.045 (4)	0.035 (4)	0.028 (3)	0.011 (3)	0.018 (3)	0.010 (3)
C5D	0.036 (3)	0.031 (3)	0.027 (3)	0.009 (3)	0.012 (3)	0.012 (3)
C6D	0.026 (3)	0.028 (3)	0.027 (3)	0.007 (2)	0.011 (2)	0.006 (2)
C7D	0.022 (3)	0.020 (3)	0.022 (3)	0.003 (2)	0.010 (2)	0.004 (2)
C8D	0.019 (3)	0.024 (3)	0.026 (3)	0.002 (2)	0.009 (2)	0.004 (2)
C9D	0.025 (3)	0.023 (3)	0.026 (3)	−0.001 (2)	0.010 (2)	−0.002 (2)
C10D	0.032 (3)	0.023 (3)	0.027 (3)	−0.001 (2)	0.012 (2)	−0.004 (2)
C11D	0.031 (3)	0.032 (3)	0.027 (3)	0.002 (3)	0.011 (2)	−0.001 (3)
C12D	0.029 (3)	0.020 (3)	0.028 (3)	0.001 (2)	0.012 (2)	0.007 (2)
C13D	0.022 (3)	0.019 (3)	0.033 (3)	−0.002 (2)	0.010 (2)	−0.005 (2)
C14D	0.049 (4)	0.036 (4)	0.027 (3)	0.003 (3)	0.010 (3)	0.009 (3)

Geometric parameters (Å, º)

O1A—C13A	1.345 (6)	O1C—C13C	1.360 (6)
O1A—H1AB	0.8200	O1C—H1CA	0.8200
O2A—C12A	1.379 (6)	O2C—C12C	1.384 (7)
O2A—C14A	1.427 (7)	O2C—C14C	1.430 (7)
N1A—C7A	1.368 (7)	N1C—C7C	1.359 (7)
N1A—C6A	1.389 (7)	N1C—C6C	1.385 (7)
N1A—H1AA	0.8600	N1C—H1CB	0.8600
N2A—C7A	1.321 (7)	N2C—C7C	1.337 (7)
N2A—C1A	1.396 (7)	N2C—C1C	1.400 (7)
C1A—C6A	1.393 (8)	C1C—C2C	1.384 (8)
C1A—C2A	1.396 (8)	C1C—C6C	1.404 (8)
C2A—C3A	1.385 (9)	C2C—C3C	1.376 (8)
C2A—H2AB	0.9300	C2C—H2CB	0.9300
C3A—C4A	1.399 (9)	C3C—C4C	1.413 (8)
C3A—H3AA	0.9300	C3C—H3CA	0.9300
C4A—C5A	1.387 (9)	C4C—C5C	1.374 (8)
C4A—H4AA	0.9300	C4C—H4CA	0.9300
C5A—C6A	1.385 (8)	C5C—C6C	1.388 (8)
C5A—H5AA	0.9300	C5C—H5CA	0.9300
C7A—C8A	1.457 (8)	C7C—C8C	1.446 (7)
C8A—C13A	1.394 (8)	C8C—C9C	1.396 (8)
C8A—C9A	1.408 (8)	C8C—C13C	1.398 (7)
C9A—C10A	1.365 (8)	C9C—C10C	1.384 (8)
C9A—H9AA	0.9300	C9C—H9CA	0.9300
C10A—C11A	1.383 (8)	C10C—C11C	1.385 (8)
C10A—H10A	0.9300	C10C—H10C	0.9300
C11A—C12A	1.378 (8)	C11C—C12C	1.357 (8)
C11A—H11A	0.9300	C11C—H11C	0.9300
C12A—C13A	1.410 (8)	C12C—C13C	1.402 (8)
C14A—H14A	0.9600	C14C—H14G	0.9600
C14A—H14B	0.9600	C14C—H14H	0.9600
C14A—H14C	0.9600	C14C—H14I	0.9600
O1B—C13B	1.362 (6)	O1D—C13D	1.367 (6)
O1B—H1BA	0.8200	O1D—H1DA	0.8200
O2B—C12B	1.374 (6)	O2D—C12D	1.372 (6)
O2B—C14B	1.428 (7)	O2D—C14D	1.417 (6)
N1B—C7B	1.357 (7)	N1D—C7D	1.361 (6)
N1B—C6B	1.389 (7)	N1D—C6D	1.391 (7)
N1B—H1BB	0.8600	N1D—H1DB	0.8600
N2B—C7B	1.327 (7)	N2D—C7D	1.311 (7)
N2B—C1B	1.397 (7)	N2D—C1D	1.405 (6)
C1B—C2B	1.391 (8)	C1D—C2D	1.374 (7)
C1B—C6B	1.403 (8)	C1D—C6D	1.389 (7)
C2B—C3B	1.375 (8)	C2D—C3D	1.398 (8)
C2B—H2BB	0.9300	C2D—H2DB	0.9300
C3B—C4B	1.393 (9)	C3D—C4D	1.399 (8)
C3B—H3BA	0.9300	C3D—H3DA	0.9300
C4B—C5B	1.382 (9)	C4D—C5D	1.396 (8)
C4B—H4BA	0.9300	C4D—H4DA	0.9300
C5B—C6B	1.385 (8)	C5D—C6D	1.392 (7)
C5B—H5BA	0.9300	C5D—H5DA	0.9300
C7B—C8B	1.464 (7)	C7D—C8D	1.470 (7)
C8B—C13B	1.392 (7)	C8D—C13D	1.396 (7)
C8B—C9B	1.400 (7)	C8D—C9D	1.400 (7)
C9B—C10B	1.375 (8)	C9D—C10D	1.374 (7)
C9B—H9BA	0.9300	C9D—H9DA	0.9300
C10B—C11B	1.374 (8)	C10D—C11D	1.388 (8)
C10B—H10B	0.9300	C10D—H10D	0.9300
C11B—C12B	1.382 (8)	C11D—C12D	1.380 (8)
C11B—H11B	0.9300	C11D—H11D	0.9300
C12B—C13B	1.396 (7)	C12D—C13D	1.400 (7)
C14B—H14D	0.9600	C14D—H14J	0.9600
C14B—H14E	0.9600	C14D—H14K	0.9600
C14B—H14F	0.9600	C14D—H14L	0.9600
C13A—O1A—H1AB	109.5	C13C—O1C—H1CA	109.5
C12A—O2A—C14A	117.0 (5)	C12C—O2C—C14C	116.4 (5)
C7A—N1A—C6A	107.0 (5)	C7C—N1C—C6C	108.4 (5)
C7A—N1A—H1AA	126.5	C7C—N1C—H1CB	125.8
C6A—N1A—H1AA	126.5	C6C—N1C—H1CB	125.8
C7A—N2A—C1A	105.4 (4)	C7C—N2C—C1C	106.2 (4)
C6A—C1A—N2A	109.6 (5)	C2C—C1C—N2C	131.3 (5)
C6A—C1A—C2A	120.1 (5)	C2C—C1C—C6C	119.9 (5)
N2A—C1A—C2A	130.3 (5)	N2C—C1C—C6C	108.8 (5)
C3A—C2A—C1A	116.7 (6)	C3C—C2C—C1C	117.8 (6)
C3A—C2A—H2AB	121.6	C3C—C2C—H2CB	121.1
C1A—C2A—H2AB	121.6	C1C—C2C—H2CB	121.1
C2A—C3A—C4A	122.2 (6)	C2C—C3C—C4C	121.4 (6)
C2A—C3A—H3AA	118.9	C2C—C3C—H3CA	119.3
C4A—C3A—H3AA	118.9	C4C—C3C—H3CA	119.3
C5A—C4A—C3A	121.7 (6)	C5C—C4C—C3C	121.8 (6)
C5A—C4A—H4AA	119.2	C5C—C4C—H4CA	119.1
C3A—C4A—H4AA	119.2	C3C—C4C—H4CA	119.1
C6A—C5A—C4A	115.5 (6)	C4C—C5C—C6C	115.9 (5)
C6A—C5A—H5AA	122.2	C4C—C5C—H5CA	122.1
C4A—C5A—H5AA	122.2	C6C—C5C—H5CA	122.1
C5A—C6A—N1A	130.6 (5)	N1C—C6C—C5C	131.4 (5)
C5A—C6A—C1A	123.8 (5)	N1C—C6C—C1C	105.4 (5)
N1A—C6A—C1A	105.5 (5)	C5C—C6C—C1C	123.2 (5)
N2A—C7A—N1A	112.4 (5)	N2C—C7C—N1C	111.1 (5)
N2A—C7A—C8A	123.9 (5)	N2C—C7C—C8C	123.9 (5)
N1A—C7A—C8A	123.6 (5)	N1C—C7C—C8C	125.0 (5)
C13A—C8A—C9A	119.2 (5)	C9C—C8C—C13C	118.8 (5)
C13A—C8A—C7A	118.0 (5)	C9C—C8C—C7C	121.8 (5)
C9A—C8A—C7A	122.8 (5)	C13C—C8C—C7C	119.4 (5)
C10A—C9A—C8A	119.7 (5)	C10C—C9C—C8C	120.3 (5)
C10A—C9A—H9AA	120.1	C10C—C9C—H9CA	119.9
C8A—C9A—H9AA	120.1	C8C—C9C—H9CA	119.9
C9A—C10A—C11A	122.0 (5)	C9C—C10C—C11C	120.1 (6)
C9A—C10A—H10A	119.0	C9C—C10C—H10C	119.9
C11A—C10A—H10A	119.0	C11C—C10C—H10C	119.9
C12A—C11A—C10A	118.9 (5)	C12C—C11C—C10C	120.7 (5)
C12A—C11A—H11A	120.6	C12C—C11C—H11C	119.7
C10A—C11A—H11A	120.6	C10C—C11C—H11C	119.7
C11A—C12A—O2A	125.0 (5)	C11C—C12C—O2C	125.3 (5)
C11A—C12A—C13A	120.7 (5)	C11C—C12C—C13C	120.1 (5)
O2A—C12A—C13A	114.3 (5)	O2C—C12C—C13C	114.6 (5)
O1A—C13A—C8A	123.7 (5)	O1C—C13C—C8C	122.4 (5)
O1A—C13A—C12A	116.8 (5)	O1C—C13C—C12C	117.5 (5)
C8A—C13A—C12A	119.5 (5)	C8C—C13C—C12C	120.1 (5)
O2A—C14A—H14A	109.5	O2C—C14C—H14G	109.5
O2A—C14A—H14B	109.5	O2C—C14C—H14H	109.5
H14A—C14A—H14B	109.5	H14G—C14C—H14H	109.5
O2A—C14A—H14C	109.5	O2C—C14C—H14I	109.5
H14A—C14A—H14C	109.5	H14G—C14C—H14I	109.5
H14B—C14A—H14C	109.5	H14H—C14C—H14I	109.5
C13B—O1B—H1BA	109.5	C13D—O1D—H1DA	109.5
C12B—O2B—C14B	116.7 (4)	C12D—O2D—C14D	116.6 (4)
C7B—N1B—C6B	107.5 (4)	C7D—N1D—C6D	106.6 (4)
C7B—N1B—H1BB	126.2	C7D—N1D—H1DB	126.7
C6B—N1B—H1BB	126.2	C6D—N1D—H1DB	126.7
C7B—N2B—C1B	105.6 (4)	C7D—N2D—C1D	106.5 (4)
C2B—C1B—N2B	130.0 (5)	C2D—C1D—C6D	121.7 (5)
C2B—C1B—C6B	120.8 (5)	C2D—C1D—N2D	130.3 (5)
N2B—C1B—C6B	109.2 (5)	C6D—C1D—N2D	108.0 (5)
C3B—C2B—C1B	117.3 (6)	C1D—C2D—C3D	116.4 (5)
C3B—C2B—H2BB	121.3	C1D—C2D—H2DB	121.8
C1B—C2B—H2BB	121.3	C3D—C2D—H2DB	121.8
C2B—C3B—C4B	121.2 (6)	C2D—C3D—C4D	121.8 (5)
C2B—C3B—H3BA	119.4	C2D—C3D—H3DA	119.1
C4B—C3B—H3BA	119.4	C4D—C3D—H3DA	119.1
C5B—C4B—C3B	122.6 (6)	C5D—C4D—C3D	121.8 (5)
C5B—C4B—H4BA	118.7	C5D—C4D—H4DA	119.1
C3B—C4B—H4BA	118.7	C3D—C4D—H4DA	119.1
C4B—C5B—C6B	116.0 (6)	C6D—C5D—C4D	115.2 (5)
C4B—C5B—H5BA	122.0	C6D—C5D—H5DA	122.4
C6B—C5B—H5BA	122.0	C4D—C5D—H5DA	122.4
C5B—C6B—N1B	132.6 (5)	C1D—C6D—N1D	106.6 (5)
C5B—C6B—C1B	122.0 (6)	C1D—C6D—C5D	123.1 (5)
N1B—C6B—C1B	105.4 (5)	N1D—C6D—C5D	130.3 (5)
N2B—C7B—N1B	112.3 (5)	N2D—C7D—N1D	112.3 (4)
N2B—C7B—C8B	122.6 (5)	N2D—C7D—C8D	123.2 (4)
N1B—C7B—C8B	125.1 (5)	N1D—C7D—C8D	124.4 (5)
C13B—C8B—C9B	118.9 (5)	C13D—C8D—C9D	119.3 (5)
C13B—C8B—C7B	118.3 (5)	C13D—C8D—C7D	117.8 (5)
C9B—C8B—C7B	122.8 (5)	C9D—C8D—C7D	122.9 (5)
C10B—C9B—C8B	119.6 (5)	C10D—C9D—C8D	120.1 (5)
C10B—C9B—H9BA	120.2	C10D—C9D—H9DA	120.0
C8B—C9B—H9BA	120.2	C8D—C9D—H9DA	120.0
C11B—C10B—C9B	121.7 (5)	C9D—C10D—C11D	120.8 (5)
C11B—C10B—H10B	119.2	C9D—C10D—H10D	119.6
C9B—C10B—H10B	119.2	C11D—C10D—H10D	119.6
C10B—C11B—C12B	119.5 (5)	C12D—C11D—C10D	119.9 (5)
C10B—C11B—H11B	120.2	C12D—C11D—H11D	120.0
C12B—C11B—H11B	120.2	C10D—C11D—H11D	120.0
O2B—C12B—C11B	126.3 (5)	O2D—C12D—C11D	125.8 (5)
O2B—C12B—C13B	114.0 (5)	O2D—C12D—C13D	114.2 (5)
C11B—C12B—C13B	119.7 (5)	C11D—C12D—C13D	120.0 (5)
O1B—C13B—C8B	123.0 (5)	O1D—C13D—C8D	122.8 (5)
O1B—C13B—C12B	116.4 (5)	O1D—C13D—C12D	117.3 (5)
C8B—C13B—C12B	120.5 (5)	C8D—C13D—C12D	120.0 (5)
O2B—C14B—H14D	109.5	O2D—C14D—H14J	109.5
O2B—C14B—H14E	109.5	O2D—C14D—H14K	109.5
H14D—C14B—H14E	109.5	H14J—C14D—H14K	109.5
O2B—C14B—H14F	109.5	O2D—C14D—H14L	109.5
H14D—C14B—H14F	109.5	H14J—C14D—H14L	109.5
H14E—C14B—H14F	109.5	H14K—C14D—H14L	109.5
C7A—N2A—C1A—C6A	0.3 (6)	C7C—N2C—C1C—C2C	−178.1 (6)
C7A—N2A—C1A—C2A	−178.3 (6)	C7C—N2C—C1C—C6C	0.3 (6)
C6A—C1A—C2A—C3A	0.0 (8)	N2C—C1C—C2C—C3C	178.2 (6)
N2A—C1A—C2A—C3A	178.5 (6)	C6C—C1C—C2C—C3C	−0.1 (9)
C1A—C2A—C3A—C4A	0.2 (9)	C1C—C2C—C3C—C4C	0.3 (10)
C2A—C3A—C4A—C5A	0.3 (11)	C2C—C3C—C4C—C5C	−0.6 (10)
C3A—C4A—C5A—C6A	−1.0 (9)	C3C—C4C—C5C—C6C	0.6 (9)
C4A—C5A—C6A—N1A	−178.4 (6)	C7C—N1C—C6C—C5C	177.9 (6)
C4A—C5A—C6A—C1A	1.2 (9)	C7C—N1C—C6C—C1C	−0.9 (6)
C7A—N1A—C6A—C5A	179.1 (6)	C4C—C5C—C6C—N1C	−178.9 (6)
C7A—N1A—C6A—C1A	−0.7 (6)	C4C—C5C—C6C—C1C	−0.3 (9)
N2A—C1A—C6A—C5A	−179.5 (5)	C2C—C1C—C6C—N1C	179.0 (5)
C2A—C1A—C6A—C5A	−0.8 (9)	N2C—C1C—C6C—N1C	0.4 (6)
N2A—C1A—C6A—N1A	0.2 (6)	C2C—C1C—C6C—C5C	0.1 (9)
C2A—C1A—C6A—N1A	179.0 (5)	N2C—C1C—C6C—C5C	−178.5 (5)
C1A—N2A—C7A—N1A	−0.8 (6)	C1C—N2C—C7C—N1C	−0.9 (6)
C1A—N2A—C7A—C8A	−177.2 (5)	C1C—N2C—C7C—C8C	−179.5 (5)
C6A—N1A—C7A—N2A	0.9 (6)	C6C—N1C—C7C—N2C	1.1 (6)
C6A—N1A—C7A—C8A	177.4 (5)	C6C—N1C—C7C—C8C	179.7 (5)
N2A—C7A—C8A—C13A	2.5 (8)	N2C—C7C—C8C—C9C	177.1 (5)
N1A—C7A—C8A—C13A	−173.6 (5)	N1C—C7C—C8C—C9C	−1.3 (8)
N2A—C7A—C8A—C9A	−179.3 (5)	N2C—C7C—C8C—C13C	−2.7 (8)
N1A—C7A—C8A—C9A	4.7 (8)	N1C—C7C—C8C—C13C	178.8 (5)
C13A—C8A—C9A—C10A	0.8 (8)	C13C—C8C—C9C—C10C	1.1 (8)
C7A—C8A—C9A—C10A	−177.4 (5)	C7C—C8C—C9C—C10C	−178.8 (5)
C8A—C9A—C10A—C11A	0.1 (8)	C8C—C9C—C10C—C11C	−0.9 (9)
C9A—C10A—C11A—C12A	−0.3 (8)	C9C—C10C—C11C—C12C	0.3 (9)
C10A—C11A—C12A—O2A	179.9 (5)	C10C—C11C—C12C—O2C	−179.6 (6)
C10A—C11A—C12A—C13A	−0.4 (8)	C10C—C11C—C12C—C13C	0.1 (9)
C14A—O2A—C12A—C11A	−7.8 (8)	C14C—O2C—C12C—C11C	−4.0 (9)
C14A—O2A—C12A—C13A	172.5 (5)	C14C—O2C—C12C—C13C	176.4 (5)
C9A—C8A—C13A—O1A	179.2 (5)	C9C—C8C—C13C—O1C	−179.8 (5)
C7A—C8A—C13A—O1A	−2.5 (7)	C7C—C8C—C13C—O1C	0.0 (8)
C9A—C8A—C13A—C12A	−1.5 (7)	C9C—C8C—C13C—C12C	−0.7 (8)
C7A—C8A—C13A—C12A	176.8 (5)	C7C—C8C—C13C—C12C	179.2 (5)
C11A—C12A—C13A—O1A	−179.4 (5)	C11C—C12C—C13C—O1C	179.3 (5)
O2A—C12A—C13A—O1A	0.3 (7)	O2C—C12C—C13C—O1C	−1.0 (7)
C11A—C12A—C13A—C8A	1.3 (8)	C11C—C12C—C13C—C8C	0.1 (8)
O2A—C12A—C13A—C8A	−179.0 (5)	O2C—C12C—C13C—C8C	179.8 (5)
C7B—N2B—C1B—C2B	−178.7 (6)	C7D—N2D—C1D—C2D	178.2 (6)
C7B—N2B—C1B—C6B	0.6 (6)	C7D—N2D—C1D—C6D	0.0 (6)
N2B—C1B—C2B—C3B	179.6 (5)	C6D—C1D—C2D—C3D	−0.7 (8)
C6B—C1B—C2B—C3B	0.3 (8)	N2D—C1D—C2D—C3D	−178.7 (5)
C1B—C2B—C3B—C4B	1.4 (9)	C1D—C2D—C3D—C4D	0.0 (9)
C2B—C3B—C4B—C5B	−2.0 (10)	C2D—C3D—C4D—C5D	1.0 (10)
C3B—C4B—C5B—C6B	0.6 (9)	C3D—C4D—C5D—C6D	−1.3 (9)
C4B—C5B—C6B—N1B	−179.9 (5)	C2D—C1D—C6D—N1D	−177.5 (5)
C4B—C5B—C6B—C1B	1.2 (8)	N2D—C1D—C6D—N1D	0.9 (6)
C7B—N1B—C6B—C5B	−179.2 (6)	C2D—C1D—C6D—C5D	0.4 (9)
C7B—N1B—C6B—C1B	−0.2 (6)	N2D—C1D—C6D—C5D	178.8 (5)
C2B—C1B—C6B—C5B	−1.7 (9)	C7D—N1D—C6D—C1D	−1.4 (6)
N2B—C1B—C6B—C5B	178.9 (5)	C7D—N1D—C6D—C5D	−179.1 (6)
C2B—C1B—C6B—N1B	179.1 (5)	C4D—C5D—C6D—C1D	0.6 (8)
N2B—C1B—C6B—N1B	−0.3 (6)	C4D—C5D—C6D—N1D	178.0 (5)
C1B—N2B—C7B—N1B	−0.8 (6)	C1D—N2D—C7D—N1D	−0.9 (6)
C1B—N2B—C7B—C8B	−179.8 (4)	C1D—N2D—C7D—C8D	−178.1 (5)
C6B—N1B—C7B—N2B	0.6 (6)	C6D—N1D—C7D—N2D	1.5 (6)
C6B—N1B—C7B—C8B	179.6 (5)	C6D—N1D—C7D—C8D	178.6 (5)
N2B—C7B—C8B—C13B	3.0 (7)	N2D—C7D—C8D—C13D	−3.3 (7)
N1B—C7B—C8B—C13B	−175.9 (5)	N1D—C7D—C8D—C13D	179.8 (5)
N2B—C7B—C8B—C9B	−177.5 (5)	N2D—C7D—C8D—C9D	174.5 (5)
N1B—C7B—C8B—C9B	3.6 (8)	N1D—C7D—C8D—C9D	−2.4 (8)
C13B—C8B—C9B—C10B	0.2 (7)	C13D—C8D—C9D—C10D	−1.0 (7)
C7B—C8B—C9B—C10B	−179.3 (5)	C7D—C8D—C9D—C10D	−178.8 (5)
C8B—C9B—C10B—C11B	1.6 (8)	C8D—C9D—C10D—C11D	1.7 (8)
C9B—C10B—C11B—C12B	−1.2 (8)	C9D—C10D—C11D—C12D	−0.7 (8)
C14B—O2B—C12B—C11B	−7.7 (8)	C14D—O2D—C12D—C11D	−0.1 (8)
C14B—O2B—C12B—C13B	173.4 (5)	C14D—O2D—C12D—C13D	179.6 (5)
C10B—C11B—C12B—O2B	−179.9 (5)	C10D—C11D—C12D—O2D	178.5 (5)
C10B—C11B—C12B—C13B	−1.0 (8)	C10D—C11D—C12D—C13D	−1.2 (8)
C9B—C8B—C13B—O1B	177.2 (5)	C9D—C8D—C13D—O1D	179.9 (5)
C7B—C8B—C13B—O1B	−3.3 (7)	C7D—C8D—C13D—O1D	−2.2 (7)
C9B—C8B—C13B—C12B	−2.4 (7)	C9D—C8D—C13D—C12D	−0.8 (7)
C7B—C8B—C13B—C12B	177.1 (5)	C7D—C8D—C13D—C12D	177.0 (5)
O2B—C12B—C13B—O1B	2.2 (7)	O2D—C12D—C13D—O1D	1.5 (7)
C11B—C12B—C13B—O1B	−176.8 (5)	C11D—C12D—C13D—O1D	−178.8 (5)
O2B—C12B—C13B—C8B	−178.1 (5)	O2D—C12D—C13D—C8D	−177.8 (5)
C11B—C12B—C13B—C8B	2.8 (8)	C11D—C12D—C13D—C8D	1.9 (8)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1AB···N2A	0.82	1.84	2.577 (6)	148
N1A—H1AA···O1D^i	0.86	2.06	2.821 (6)	147
N1A—H1AA···O2D^i	0.86	2.56	3.220 (6)	135
O1B—H1BA···N2B	0.82	1.81	2.546 (6)	149
N1B—H1BB···O1C^ii	0.86	2.10	2.813 (6)	140
O1C—H1CA···N2C	0.82	1.85	2.592 (6)	149
N1C—H1CB···O1B^iii	0.86	2.08	2.844 (6)	148
N1C—H1CB···O2B^iii	0.86	2.50	3.108 (6)	128
O1D—H1DA···N2D	0.82	1.81	2.547 (5)	148
N1D—H1DB···O1A^iv	0.86	2.12	2.832 (6)	140
N1D—H1DB···O2A^iv	0.86	2.45	3.149 (6)	139
C3B—H3BA···Cg1^v	0.93	3.03	3.815 (7)	143
C14A—H14C···Cg2^i	0.96	3.07	3.777 (7)	131
C14B—H14E···Cg3^i	0.96	2.93	3.417 (7)	112
C14D—H14K···Cg4^vi	0.96	3.04	3.775 (6)	134
C3C—H3CA···Cg5^vii	0.93	2.80	3.562 (6)	140

Symmetry codes: (i) −x+1, y, −z+1/2; (ii) −x, y, −z+1/2; (iii) x, y−1, z; (iv) x, y+1, z; (v) x−1, y, z; (vi) x, −y+1, z+1/2; (vii) −x, −y+1, −z+1.